(+)-Vitisin C

Details

• Internal ID: 237dba1a-94c6-473d-8b5b-425a0a38a5a8
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2S,3S)-4-[(E)-2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(C=C(C=C3O2)O)C=CC4=CC5=C(C=C4)OC(C5C6=C7C(C(OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C3=C(C=C(C=C3O2)O)/C=C/C4=CC5=C(C=C4)O[C@H]([C@H]5C6=C7[C@@H]([C@H](OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• InChI: InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55+,56-/m0/s1
• InChI Key: WZKKRZSJTLGPHH-WHSOPTDBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₄₂O₁₂
• Molecular Weight: 906.90 g/mol
• Exact Mass: 906.26762677 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 10.00

Synonyms

• (+)-vitisin C
• 180580-73-8
• M2HXT5SWE2
• DTXSID10583213
• 5-[(2S,3S)-4-[(E)-2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• 5-((2S,3S)-4-((E)-2-((2R,3S)-3-((2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl)ethenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl)benzene-1,3-diol
• RefChem:67561
• DTXCID90533978
• 5-((2S,3S)-4-((E)-2-((3S)-3-((3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl)ethenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl)benzene-1,3-diol
• 1,3-Benzenediol, 5-((2R,2S,3S,3S)-5-((1E)-2-((2S,3S)-3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-
• 5-((2R,2S,3S,3S)-5-((1E)-2-((2S,3S)-3-(3,5-Dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-1,3-benzenediol
• UNII-M2HXT5SWE2
• CHEMBL442911
• CHEBI:192464
• Q7937134
• 1,3-BENZENEDIOL, 5-(5-(2-(3-(3,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-BENZOFURANYL)ETHENYL)-2,2,3,3-TETRAHYDRO-6-HYDROXY-2,2-BIS(4-HYDROXYPHENYL)(3,4-BIBENZOFURAN)-3-YL)-, (2S-(2.ALPHA.,3.BETA.,4(E(2S*,3R*(2R*,3R*)))))-
• 1,3-Benzenediol, 5-(5-(2-(3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-, (2S-(2alpha,3beta,4(E(2S*,3R*(2R*,3R*)))))-
• 5-[(2S,3S)-4-[(E)-2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.96%	91.11%
CHEMBL3194	P02766	Transthyretin	92.87%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	90.97%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.33%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.28%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.15%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	86.06%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.31%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.15%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.13%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.09%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	81.75%	83.82%
CHEMBL2581	P07339	Cathepsin D	81.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.74%	99.17%

Plants that contains it

• Acacia adunca
• Aconitum burnatii
• Adiantum philippense
• Annona cornifolia
• Artemisia campestris subsp. variabilis
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Pseudocydonia sinensis
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Viguiera incana
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 16145527
• NPASS: NPC6702
• ChEMBL: CHEMBL442911
• LOTUS: LTS0199778
• wikiData: Q7937134